My second first paid blowjob

Several years after the blowjob I wrote about here, I paid for my second first blowjob. This one was radically different from the first in every way. (You need to read my origin myth, here, here, and here to get a feel for my current stance vis-a-vis what follows, if you haven’t. And you may as well read all this.) And I should say – in between, there were (I just discovered by re-reading my journal) a few paid blowjobs of which I have no memory – blowjobs provided by “escorts” I hired in cities in which I was traveling. All awful. But I didn’t remember these (and only do very vaguely even after having read my own notes to myself about them at the time). So this one, the one I’m writing about here, was, from an important standpoint, my second first paid blowjob. It certainly marked an inflection point in the way that those others didn’t.

It was a weekday afternoon, and I wanted to play hookie from work for a bit, to get a handjob that was a little… special. By this time, I was going almost daily to one or another of the half-dozen or so “rub-and-tug” places that I frequented (and described here). I had discovered the slightly more upscale, more expensive form of “sensual massage” prevalent in the “tantra” section of Eros – a website devoted to matching up customers with sex workers. These massages tend to cost about 50% more, but to be conducted by individual, independent professionals, operating out of their own homes or studios. They tend to be women who genuinely seem to like their work (and who seem to think it vitally important). They take themselves, their work, very seriously – and often are at pains not to be simply providers of sensual massages, but rather “tantrikas,” “sacred muses,” or some other such title.

I had seen such a woman – I forget her name – a number of times, and it was to her that I turned this afternoon (in the Fall of 2004, I believe). This woman, unfortunately, reported (when I reached her on her cell phone) that she was out of town, that she couldn’t help me. “But,” she said, “I have a friend – Isabella – who’s new to this work, but who’s looking for clients.”

I called Isabella, the woman to whom I’d been referred. She told me she’d love to see me, but that she didn’t have a great place to conduct a session – I’d have to visit the apartment she was housesitting.

I made my way to a sixth-floor walk-up in a tenement in Alphabet City. Isabella opened the door, and was exactly as described. “I’m Amy,” she said, offering her hand. “I mean Isabella!” she added.

She was exactly as described. Blonde, slightly freckled, lithe, petite. Her hair was a little stringy. I didn’t think, “What a babe.” What I thought was, “This is an attractive woman.”

We chatted for a few minutes – she offered me water. She was visibly anxious. I was, she told me, her first-ever client. To this (by-then) expert on the frequent lies and games of sex workers, her claim seemed plausible.

She laid a towel on her bed, and invited me to lie down on my stomach. On this occasion, as I recall, I successfully mustered the courage to request “an early flip” – that she turn me over onto my back and tend to my cock earlier than 30-45 minutes into the session. She seemed pleased – I think she may even have said something like, “Oh, goodie!” I closed my eyes, and she started massaging my cock expertly with some AstroGlide. I closed my eyes, my head lolled back.

As I lay there, relaxing, enjoying, I felt a shock: her mouth descended on my cock. “STOP!” I said. “What are you doing?”

“I thought you would want this,” she said.

“NO!” I said

“Really?”

She was incredulous. I think I may have been too.

Again – the specifics are hazy, but I’m reasonably confident that she said something to the effect of, “Ok – don’t think of this as part of the massage. Think of this as something I want to do.”

And without waiting for my assent, she swallowed me again. My resolve had weakened somewhat, and, to be honest, while I easily could resist a woman asking me to pay, this was a different matter: she was my kryptonite – a woman who professed genuine free-standing desire for me.

That’s not all – we went WAY over the hour and she wouldn’t take extra money.

In short: she communicated genuine desire for me. Over the coming months, I found myself increasingly unable to resist her, even as my wife’s pregnancy advanced and, ultimately, our child was born. Our meetings grew more frequent – every other week or so, at their peak. (They were subject to the logistical challenge of her finding a friend’s apartment we could use.)

She taught me a lot: she asked me to push her head down (something I’d never done before, and that took a lot of learning); she role-played – a French nun, a Japanese schoolgirl, a horny housewife, an American teenaged slut, a whore (her word); we experimented with compensation – how did it feel different when I paid her $5? $50? $500?

I never did anything other than collect her blowjobs. I didn’t kiss her, didn’t touch her pussy (though I would tell myself that I would touch her pussy before each meeting – I never got up the courage), certainly never fucked her. I didn’t go down on her, either. No, she was just a happy provider of blowjobs to me: blowjobs that lasted an hour, two hours, even three hours. She loved sucking my dick almost as much as I loved having her on it. She confessed that for her, the money had nothing to do with me: she just loved the feeling of being paid. AND she liked sucking my cock. So this was a fortuitous coincidence: I had a great cock, one she could suck for hours, AND I would pay her.

About six or nine months after we started seeing one another, she told me that we had to stop. She had fallen in love, she said, with someone who simply wouldn’t understand or tolerate our relationship.

This was a lonely-making event for me: I too was in love with someone who wouldn’t understand or tolerate our relationship. I was married to her. That didn’t stop me from seeing her. It grated me just a bit – made me feel she was claiming some sort of superiority. Where clearly, in fact, she was simply demonstrating greater honorability.

We had a final conversation – a debrief in which we learned the “real” details of one another’s “real” lives. Without going into those details, suffice it to say, we have a lot of friends in common in Facebook (though we never have seen one another again).

Sadly, Isabella’s graduation from sex work didn’t have the same impact on me: my oral cherry had been popped. I no longer feared the stigma of crossing that particular line. The logic of addiction, of deception, is simple: once you’ve done something once, once you’ve created a secret of some magnitude, the incremental cost (in shame, in self-esteem) of repeating the sin, extending the lie, is almost infinitely smaller than it is in the first instance.

This is why pimps “turn out” prostitutes. Once they’ve done it, they no longer can say they never did (honestly). And is twice really worse than once? Not in this realm, it turns out.

Isabella moved onward and upward; I continued on the path I’ve been describing. More blowjobs, from women who were less pleasing – in every way.

Damn. You are such a good writer. And again I’m breathless, but not in a turned on sort of way. In a holy fuck I can’t believe what I just read sort of way. Maybe it’s my naivete and inexperience and I’m just shocked. I don’t know. But it’s something.